Tucked away in the verdant hills of Gingerland, the colourful Golden Rock Inn has an enchanted-garden feel. Once a 19th-century sugar estate with a cluster of stone buildings and 100 acres of rampant forest, it was rescued and transformed six years ago by New York-based artists Brice and Helen Marden. The old counting house is now the foliage-framed reception, and architect Ed Tuttle (well known for his work with Aman Resorts) designed the dining areas and restaurant terrace where, surrounded by serene reflection pools, you can feast on jerk pork with pineapple relish or mahi-mahi in red coconut curry sauce. Miami-based landscape architect Raymond Jungles coaxed the grounds into a wild, freewheeling maze of bamboo trees and boulders, palms, orchids and exuberant tropical flora where dragonflies and hummingbirds flutter past. The Mardens have added their own artistic touches, too: bright red gates, a monochrome-striped floor around the Olympic-sized pool, and contemporary sofas by designers including Patricia Urquiola and the Campana Brothers in the public spaces. The 11 cottages vary in style: one is a two-storey suite in the thimble-shaped mill; some have blond-wood floors and Moroccan rugs, others have avocado-coloured concrete verandahs, bamboo four-posters or Peruvian wool blankets by John Derian. None of them have air-con, TVs or minibars. It's hip but low-fi, a sanctuary where even Anna Wintour has been known to decamp over Christmas to escape and unwind.

Islanders travel miles to the old seaside fort in the fishing village of Shermans to eat at this hotel's restaurant, The Fish Pot. The most sought-after seats in the house are those overlooking the sea, particularly at sunset when you can order lobster, grilled prawns and mahi-mahi while watching the sky slowly turn from fuchsia to mauve. But not many regulars have cottoned on to the New England-style, sea-facing wooden cottages in the lush tropical gardens (there are also a handful of suites above the restaurant). Each has a wraparound veranda, a fully equipped kitchen and a light, airy living room filled with books and Barbadian designs. The teak beds upstairs are enormous and the bathrooms small but perfectly formed. Breakfast isn't always quite as spot-on as dinner, but the banana bread - freshly baked each morning - is delicious. There's a tiny spa and two blissful pools, the smallest in the style of a miniature Roman bath with stone columns and water features. Laze in the sun with the resident tabby cat or clamber over the rocky headland to search out hidden coves and glimpse the rock-star mansions that back onto the bay (watch out for the tide, which comes in quickly so that by early afternoon there's only a narrow strip of white sand peeking out from under the shallows). On Friday nights, the nearby Six Men's fish market is the place to go for ice-cold Carib beers and grilled meat, eaten with greasy fingers while perched on wooden benches.

This former fishing lodge, on a remote stretch of sandy beach just outside the village of Hartswell, was renovated and reopened as a hotel last year. The eight simple but elegant rooms, each named after the different shade of blue painted on the walls, are all in one main building (come with a gang of friends and book the lot). Round wooden tables are teamed with wicker chairs and lobster-print cushions; bedside lamps have smooth glass bases filled with a single flower and sand, and from white wooden balconies guests can look across the water to Little Exuma, the smaller island of the pair, linked by a one-lane bridge. Borrow kayaks and paddleboards or jump in the car to visit deserted Pelican Beach and cross the clearly marked line of the Tropic of Cancer. Or simply laze on one of the daybeds suspended over the beach, with a local Sand beer in hand, before cooling down in the freshwater infinity pool that cascades into the bay. There's a smart Peruvian-Asian restaurant, ONE80, serving fresh sushi, seafood stews and ceviche, with chilled house music, white whirring ceiling fans and an outdoor wooden deck for lounging beneath the stars. If you want to venture out in the evening, head to Santana's Grill Pit on Little Exuma, a groovy little spot that's a favourite with Johnny Depp.

In the West End of Negril, on limestone cliffs a 10-minute drive from the big-name juggernaut resorts by the beach, The Caves is one of Island Records founder Chris Blackwell's trio of Jamaican hotels (he also owns Golden Eye and Strawberry Hill). It's all-inclusive and child-free, so the rum punch flows from the minute you arrive at the green-and-blue reception hut and sink into the African graphic-print cushions. Scattered along the cliff top are 12 wooden, thatch-roofed cottages, some split-level, each painted a different colour and with its own hammock on a private sun deck. Here, it is all about the ocean: everything faces it and leads to it. If you can pluck up the courage, do as the 'jumpers' do and cool off by repeatedly leaping into the water from a 20-metre cliff. Alternatively, ask Paul, the resident diver, to take you snorkelling on Sandy Key Reef. Breakfast is served whenever, wherever (and there are no menus). Order huge platters of fruit followed by eggs, any style, and add a dash of Busha Browne's spicy jerk sauce (it tastes good on everything). For lunch and supper, there are usually two choices: perhaps freshly caught conch and salad, followed by ice creams in crazy flavours including stout or grapenut. Afterwards, climb the steep steps to the candlelit bar built out of the rocks. It's all so relaxed; hippy enough that you can wear your bikini for supper, but smart enough that you know you're in good company.

Take a short hop from mainland St Vincent to Port Elizabeth, then drive east along a potholed road. Two miles on, the groves of wild palm trees part to reveal the stone-walled Beach House at Sugar Reef. Set in 65 acres of a former coconut plantation, this hotel is like a Caribbean of yesteryear, a throwback to the 1960s. New York-based interior designer Jonathan Berger freshened up the place two years ago, and he seems to have been inspired by British theatre designer Oliver Messel, whose fabulous creations in the 1960s and 1970s defined a generation of private homes in the Caribbean. White latticework shutters frame jalousie windows and let in the warm breeze. Chef John cooks up dishes such as callaloo lasagne and the best lobster roti on the island, which are eaten beneath the enormous driftwood chandelier in the main dining room, at wooden tables facing the ocean. Of the eight bedrooms, there are three in the Beach House with Matouk linen sheets on four-poster beds, driftwood mirrors and screened French doors that swing open onto a terrace fronting the white-sand, coconut-husk-strewn Crescent Beach. The other five are about a mile uphill in the French House, with its polished mahogany and stone archways, and a wraparound veranda with a plunge pool. Cycling through the estate, kayaking or snorkelling make afternoons melt away; in the evenings, gather round and play board games to a background chorus of singing frogs. Book it

The most famous beach on Harbour Island, a spit of land three miles long and a mile wide, is Pink Sands. Here, in a certain light, the grains beneath your feet really do glow a soft, peachy colour. Parked right in the middle of it is The Dunmore, something of an institution since the 1960s. The vibe is elegant without being remotely stuffy; barefoot beach club with a touch of old-fashioned Bahamian glamour. The current owners are former guests who took over four years ago (people really do get addicted to the island) and hired Nassau- based designer Amanda Lindroth to kit out the 14 beachfront and garden cottages with teak furniture, rattan blinds and graphic-patterned cushions and throws (you can also rent the private residences when they're not in use). Laze about on monochrome-striped deckchairs by the pool or beneath turquoise umbrellas on the palm-fringed beach (despite the East Coast Americans who have been coming here for years, it never feels too crowded, even at Christmas). The restaurant produces some of the best food on the island - potter up and tuck into lobster, breadfruit fish tacos, snapper sandwiches with sweet potato or truffle fries, and a large Dark and Stormy (there's a more sophisticated menu in the evening). If you want to do more than flop, there's deep-sea fishing and kite-surfing, or hire a golf buggy and tootle down to the bayside where most of island life unfolds.

A 15-minute plane ride from Nassau but a world away from the glitz and crowds, private island Kamalame Cay is a little bit like the Mustique of 50 years ago. Owned by the Hews, a sixth-generation West Indies family who spotted it on a sailing trip in the 1990s, the island is a secluded slip of white sand edged by turquoise water, with some of the world's best and least-explored, kaleidoscopic coral gardens and a barrier reef a mile from shore. For the last two years, dashing son David and his partner Michael have been in charge, transforming this charming, little-known hotel. The bougainvillaea-draped houses sprinkled along the shores among the thousands of coconut palms have been spruced up with antiques, Balinese armchairs, seashells and well-thumbed books. There are clay tennis courts and a spa pavilion on stilts over the water, and a conch shell-lined sand pathway leads through a thicket of palms to a pool and beachfront Tiki bar, where there are often BBQs and colossal bonfires at night. In the Great House dining room, the linens are now prettier, the glassware finer. And the seriously good South Asian-influenced Bahamian food is attracting a discerning crowd, who arrive by speedboat for long Pouilly- Fuissé-fuelled lunches of fresh crab dim sum, Caprese salads with homemade buffalo mozzarella and warm bread fresh from the oven of the on-site bakery. Celebrity fans include Penélope Cruz and Nicole Kidman, and the British wing of the Weston family, who took over most of the place last Easter.

A very charming, plantation-pretty hotel, the Inn has its own crescent of sand with great views of the yachts streaming in and out of the harbours on the other side of the bluff. It may have opened in the 1960s, but this place has stayed under the radar, along an un-signposted turn-off on the climb to Shirley Heights (steel drums can be heard from tea-time on Sundays). Bordered by thick palm forest, it feels protected, yet it is in a cracking location close to all the action. Bedrooms are in painted clapboard buildings with deep verandahs, fringed with the palest blush-pink bougainvillaea. Tropical red hibiscus lines the paths and yellow-bellied bananaquit birds dive-bomb the pool. Inside, four-poster beds are curtained by soft white muslin with scalloped edges, Penhaligon's soaps sit atop mahogany washstands in the bathrooms, and rattan planter's chairs face the water. It is crisp and uncomplicated, simple and straightforward. Plans are in place to add more rooms - another 10 to the current 28 - but introduced in a slow, considered way, so as not to disturb or overcrowd. There's a great pair of floodlit tennis courts, a little spa, a boutique with rails of dresses made from gorgeous pastel-coloured thick linens, and two restaurants, one right on the beach for a club sandwich and another further up the hill. This is not a lock-you-in, all-inclusive sort of place. Which is just as well, as even though you might expect fresh spaghetti and risotto from the Italian owners, it's often lamb chops and mint sauce for supper. The fun and games of English Harbour and Nelson's Dockyard are just over the water using a shuttle boat that goes as and when you want, so you can get out and about for a bite to eat at The Admiral's Inn, a pizza at Paparazzi, or a rosé-soused afternoon at Catherine's Café Plage.

Visitors to North Beach arrive by tiny, eight-seater plane, touching down at Barbuda airport's single green shed before taking a speedboat, which arrows through the mangroves, zipping across what locals call 'the lake of glass' and round the headland. Soon, five whitewashed cottages come into view, sitting on stilts above an emerald lagoon. A conch-sprinkled stretch of sand acts as reception, the translucent sea is the pool and Douglas, the resident donkey, the easygoing concierge. The beach rules - no iPhones, no internet, no interruptions - provoke instant Caribbean torpor. Sipping a Wadadli beer and gazing across the snapper-packed sea, the only disturbance is the wind rustling the palm trees and water breaking over the reef. Reuben James, North Beach's Barbudan owner, hand-built the rustic, nautical-vibe cottages over 28 years, while squeezing in work as a conductor, politician and engineer. These days he's head chef and barman, and his celebrated punch - rum, lime, grenadine, bitters and nutmeg - slips down easily with a grilled lobster supper. If swinging in a hammock gets tiring, nip to Princess Diana beach, where the K Club (Diana's former retreat from the paparazzi, owned by fashion designer Mariuccia Mandelli, who has batted away multi-million-pound offers for the lease) lies on a three-mile curve of white sand.

Easy to miss from the roadside, the white Lone Star building, now the hotel reception, still has the blue signage left over from its days as a garage. You'd never know that for the last few years this has been one of the most fashionable spots on the island. It's just got a smidge more chic thanks to its new British owner David Whelan who, last year, revamped the property, which stands alone on a pristine stretch of beach in Alleynes Bay. The restaurant, which is incredibly popular - particularly for Sunday brunch and dinner - has car-themed photography on its white walls, and staff dressed in mechanic-style boiler suits. The food is top-notch: try the snapper, blackened to perfection with just the right amount of spiciness, and the seafood pizza. Five suites with modern four-poster beds are named after classic cars and have either beachfront or garden terraces. Some, such as the Buick Suite, have a more New England feel with navy-and-white striped cushions and white slatted wardrobes; others, such as the two-bedroomed Lincoln in the Beach House, are more Ralph Lauren, with exposed brick walls, church candles and shells dotted about, and a roll-top bath in the bathroom. Work up an appetite swimming with the turtles that hatch and nest right in front of the hotel (there's no pool, but loungers on the beach are for guests only and some of the suites have private gardens) then, for lunch, stroll to Ju-Ju's beach bar for a delicious fried flying-fish sandwich.